AR035854A1 - COMPOUNDS DERIVED FROM PYRIDOPIRIMIDINE AND NAFTIRIDINE, ITS USE, A PROCEDURE TO PREPARE THEM, A COMPOSITION THAT UNDERSTANDS THEM, INTERMEDIARY COMPOUNDS AND A PROCESS TO PREPARE A SULFUR COMPOUND - Google Patents

COMPOUNDS DERIVED FROM PYRIDOPIRIMIDINE AND NAFTIRIDINE, ITS USE, A PROCEDURE TO PREPARE THEM, A COMPOSITION THAT UNDERSTANDS THEM, INTERMEDIARY COMPOUNDS AND A PROCESS TO PREPARE A SULFUR COMPOUND

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Publication number
AR035854A1
AR035854A1 ARP020100430A ARP020100430A AR035854A1 AR 035854 A1 AR035854 A1 AR 035854A1 AR P020100430 A ARP020100430 A AR P020100430A AR P020100430 A ARP020100430 A AR P020100430A AR 035854 A1 AR035854 A1 AR 035854A1
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AR
Argentina
Prior art keywords
alkyl
hydrogen
cycloalkyl
aryl
cycloalkylalkyl
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ARP020100430A
Other languages
Spanish (es)
Inventor
Jian Jeffrey Chen
James Patrick Dunn
David Michael Goldstein
Christoph Martin Stahl
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Hoffmann La Roche
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Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR035854A1 publication Critical patent/AR035854A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Abstract

Compuestos derivados de piridopirimidina y naftiridina de fórmulas (1) ó (2) o sales farmacéuticamente aceptables de los mismos, en donde: Z es N ó CH; W es NR2; X1 es O, NR4 (donde R4 es hidrógeno o alquilo), S, ó CR5R6 (donde R5 y R6 son independientemente hidrógeno o alquilo) ó C=O; X2 es O ó NR7; Ar1 es arilo o heteroarilo; R2 es hidrógeno, alquilo, acilo, alcoxicarbonilo, ariloxicarbonilo, heteroalquilcarbonilo, heteroalquiloxicarbonilo, ó -R21-R22, donde R21 es alquileno ó -C(=O)- y R22 es alquilo o alcoxilo; R1 es hidrógeno, alquilo, haloalquilo, arilo, aralquilo, heteroarilo, heteroaralquilo, cicloalquilo, cicloalquilalquilo, cicloalquilo heteroalquil sustituido, cicloalquilo heterosustituido, heteroalquilo, cianoalquilo, heterociclilo, heterociclilalquilo, R12-SO2-heterocicloamino (donde R12 es haloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo), -Y1-C(O)-Y2-R11 (donde Y1 e Y2 son independientemente uno del otro ausente o un grupo alquileno y R11 es hidrógeno, alquilo, haloalquilo, hidroxilo, alcoxilo, amino, monoalquilamino o dialquilamino), (heterociclil)(cicloalquil)alquilo o (heterociclil)(heteroaril)alquilo; R3 es hidrógeno, alquilo, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, haloalquilo, heteroalquilo, cianoalquilo, alquileno-C(O)-R31 (donde R31 es hidrógeno, alquilo, hidroxilo, alcoxilo, amino, monoalquilamino o dialquilamino), amino, monoalquilamino, dialquilamino o NR32-Y3-R33 (donde Y3 es -C(O), -C(O)O-, -C(O)NR34, S(O)2 ó S(O)2NR35; R32, R34 y R35 son independientemente hidrógeno o alquilo; y R33 es hidrógeno, alquilo, cicloalquilo, cicloalquilalquilo, heteroalquilo o fenilo opcionalmente sustituido) o acilo; R7 es hidrógeno o alquilo; y R8 y R9 son independientemente hidrógeno, alquilo, arilo, aralquilo, cicloalquilo, cicloalquilalquilo, heteroalquilo, alquilsulfonilo, arilsulfonilo, -C(O)-R81 (donde R81 es alquilo, arilo, aralquilo, cicloalquilo, cicloalquilalquilo, heteroalquilo, alcoxilo, ariloxilo, amino, mono- o di-alquilamino, arilamino, o aril(alquil)amino) ó R8 y R9 juntos forman =CR82R83 (donde R82 y R83 son independientemente hidrógeno, alquilo, cicloalquilo, cicloalquilalquilo o fenilo opcionalmente sustituido), o sales farmacéuticamente aceptables de los mismos. Uso para la preparación de un medicamento, proceso para prepararlos, composición que los comprende, compuestos intermediarios y proceso para preparar un compuesto sulfuro. Los compuestos de fórmula (1) y (2) son útiles para el tratamiento de trastornos mediados por p38, específicamente en donde el trastorno mediado por p38 es artritis, enfermedad de Crohn, síndrome de intestino irritable, síndrome de dolor respiratorio adulto o enfermedad pulmonar obstructiva crónica, o el trastorno mediado por p38 en la enfermedad de Alzheimer. Reivindicación 32: Un proceso para preparar un compuesto sulfuro de la fórmula (3), en donde Z es N ó CH; X1 es O, NR4 (donde R4 es hidrógeno o alquilo), S, CR5R6 (donde R5 y R6 son independientemente hidrógeno o alquilo) ó C=O; X2 es O; Ar1 es arilo o heteroarilo; R es alquilo o arilo; R3 es hidrógeno, alquilo, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, haloalquilo, heteroalquilo, cianoalquilo, acilo, alquileno-C(O)-R31 (donde R31 es hidrógeno, alquilo, hidroxilo, alcoxilo, amino, monoalquilamino o dialquilamino), amino, monoalquilamino, dialquilamino o NR32-Y3-R33 (donde Y3 es -C(O), -C(O)O-, -C(O)NR34, S(O)2 ó S(O)2NR35; R32, R34 y R35 son independientemente hidrógeno o alquilo; y R33 es hidrógeno, alquilo, cicloalquilo, cicloalquilalquilo, heteroalquilo o fenilo opcionalmente sustituido); dicho método comprende los pasos de: poner en contacto un aldehido de fórmula (4) con un compuesto arilo de fórmula Ar1-X1-CH2-X3, en donde X3 es -C(=O)-OR' y R' es alquilo, bajo condiciones suficientes para producir dicho compuesto de sulfuro.Compounds derived from pyridopyrimidine and naphthyridine of formulas (1) or (2) or pharmaceutically acceptable salts thereof, wherein: Z is N or CH; W is NR2; X1 is O, NR4 (where R4 is hydrogen or alkyl), S, or CR5R6 (where R5 and R6 are independently hydrogen or alkyl) or C = O; X2 is O or NR7; Ar1 is aryl or heteroaryl; R2 is hydrogen, alkyl, acyl, alkoxycarbonyl, aryloxycarbonyl, heteroalkylcarbonyl, heteroalkyloxycarbonyl, or -R21-R22, where R21 is alkylene or -C (= O) - and R22 is alkyl or alkoxy; R1 is hydrogen, alkyl, haloalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, cycloalkyl, cycloalkylalkyl, substituted heteroalkyl cycloalkyl, heteroalkyl, cyanoalkyl, heterocyclyl, heterocyclylalkyl, R12-SO2-arylalkyl, heterocycloalkyl heteroaryl or heteroaralkyl), -Y1-C (O) -Y2-R11 (where Y1 and Y2 are independently of each other absent or an alkylene group and R11 is hydrogen, alkyl, haloalkyl, hydroxyl, alkoxy, amino, monoalkylamino or dialkylamino) , (heterocyclyl) (cycloalkyl) alkyl or (heterocyclyl) (heteroaryl) alkyl; R3 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, haloalkyl, heteroalkyl, cyanoalkyl, alkylene-C (O) -R31 (where R31 is hydrogen, alkyl, hydroxyl, alkoxy, amino, monoalkylamino or dialkylamino), amino, monoalkylamino , dialkylamino or NR32-Y3-R33 (where Y3 is -C (O), -C (O) O-, -C (O) NR34, S (O) 2 or S (O) 2NR35; R32, R34 and R35 they are independently hydrogen or alkyl, and R33 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, heteroalkyl or optionally substituted phenyl) or acyl; R7 is hydrogen or alkyl; and R8 and R9 are independently hydrogen, alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heteroalkyl, alkylsulfonyl, arylsulfonyl, -C (O) -R81 (where R81 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heteroalkyl, alkoxy, aryloxy , amino, mono- or di-alkylamino, arylamino, or aryl (alkyl) amino) or R8 and R9 together form = CR82R83 (where R82 and R83 are independently hydrogen, alkyl, cycloalkyl, cycloalkylalkyl or optionally substituted phenyl), or pharmaceutically salts Acceptable of them. Use for the preparation of a medicament, process for preparing them, composition comprising them, intermediates and process for preparing a sulfide compound. The compounds of formula (1) and (2) are useful for the treatment of p38-mediated disorders, specifically where the p38-mediated disorder is arthritis, Crohn's disease, irritable bowel syndrome, adult respiratory pain syndrome or lung disease. chronic obstructive disorder, or p38 mediated disorder in Alzheimer's disease. Claim 32: A process for preparing a sulfide compound of the formula (3), wherein Z is N or CH; X1 is O, NR4 (where R4 is hydrogen or alkyl), S, CR5R6 (where R5 and R6 are independently hydrogen or alkyl) or C = O; X2 is O; Ar1 is aryl or heteroaryl; R is alkyl or aryl; R3 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, haloalkyl, heteroalkyl, cyanoalkyl, acyl, alkylene-C (O) -R31 (where R31 is hydrogen, alkyl, hydroxyl, alkoxy, amino, monoalkylamino or dialkylamino), amino , monoalkylamino, dialkylamino or NR32-Y3-R33 (where Y3 is -C (O), -C (O) O-, -C (O) NR34, S (O) 2 or S (O) 2NR35; R32, R34 and R35 are independently hydrogen or alkyl; and R33 is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, heteroalkyl or optionally substituted phenyl); said method comprises the steps of: contacting an aldehyde of formula (4) with an aryl compound of formula Ar1-X1-CH2-X3, wherein X3 is -C (= O) -OR 'and R' is alkyl, under sufficient conditions to produce said sulfide compound.

ARP020100430A 2001-02-12 2002-02-11 COMPOUNDS DERIVED FROM PYRIDOPIRIMIDINE AND NAFTIRIDINE, ITS USE, A PROCEDURE TO PREPARE THEM, A COMPOSITION THAT UNDERSTANDS THEM, INTERMEDIARY COMPOUNDS AND A PROCESS TO PREPARE A SULFUR COMPOUND AR035854A1 (en)

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US26837501P 2001-02-12 2001-02-12
US33465401P 2001-11-30 2001-11-30

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JP (1) JP4064818B2 (en)
KR (1) KR100639772B1 (en)
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AR (1) AR035854A1 (en)
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